Now Leaving: Woulda, Coulda, Shoulda
“Be very careful, then, how you live—not as unwise but as wise, making the most of every opportunity, because the days are evil.” – Ephesians 5:15-16
Many times over the course of the last 60 plus years I’ve found myself sitting and sulking in the Land of Woulda, Coulda, Shoulda.
You’ve been there, right?
You drive down the Road of Regret, go through the Grove of Guilt, and roll past the Lake of Shame. Then you head off the Cliff of Confusion and into the Ravine of Remorse. You crash into the Rocks of Sorrow, and, sitting alone amid the carnage, you gaze at your belly button and ask “what if” questions about your life.
What if I had just taken Jesus seriously when I was a teenager instead of chasing the desires of my flesh?
What if I’d spent more time on my boyhood idea to invent asphalt that would melt snow and ice on the highways?
What if I had spoken up that day in the early 1990s when God put it on my heart to share the gospel with the guy I talked to while he was cleaning tables in the convention center in Atlanta?
What if I had followed my instincts and invested in bitcoin in 2019 when I was doing some work with professors who were experts on blockchain technology?
What if I had been a better father to my children?
What if?
Here’s the reality: Our decisions to act or not act on temptations and opportunities come with consequences, positive and negative. But while those decisions and their consequences should inform our future, they don’t have to define our future.
The good thing about regret, author Daniel Pink wrote in The Power of Regret, is that “if we know what we truly regret, we know what we truly value.” Regret is a “maddening, perplexing, and undeniably real emotion,” Pink wrote, but it also “points the way to a life well lived.”
To exit the Land of Woulda, Coulda, Shoulda, we have to turn regret into something positive, and to do that I’ve found I have to do at least three things. Perhaps you can relate.
1. Get off the wrong road
“When he came to his senses, he said, ‘How many of my father’s hired servants have food to spare, and here I am starving to death! I will set out and go back to my father and say to him: Father, I have sinned against heaven and against you. I am no longer worthy to be called your son; make me like one of your hired servants.’ So he got up and went to his father.” (Luke 15:17-20a)
In Mere Christianity, C.S. Lewis points out that real progress, which we all want, means getting closer to the place we want to be. But if we’ve taken a wrong turn, then going forward doesn’t get us any nearer to our desired destination. “If you are on the wrong road,” he wrote, “progress means doing an about-turn and walking back to the right road; and in that case the man who turns back soonest is the most progressive man.”
Pastor Jon Tyson called this a picture of what it looks like to redeem our time.
“The world tells men my age to push harder, keep going, and strive,” Tyson wrote in a newsletter for Primal Path. “But sometimes, the bravest thing a man can do is stop and choose a future based on the invitation to turn back to the path of life and resolve that no matter what has gotten lost along the way, you will recover and return with the gift of your remaining days.”
2. Get on the God road
“Repent, then, and turn to God, so that your sins may be wiped out, that times of refreshing may come from the Lord,” (Acts 3:19)
James R. Sherman, in a short book he wrote in 1982, pointed out that “You can’t go back and make a new start, but you can start right now and make a brand new ending.”
To do so, of course, we not only have to get off the wrong road but we also have to get on the right road. It does no good, and in fact it can make things much worse, if we get off one wrong road only to get onto another wrong road. God’s road is the right road.
Thankfully, when we repent, He is faithful to forgive us. Through the work of the Holy Spirit, we can realign with His story for our lives and practice what Tyson referred to as “daily repentance.” “Turning back isn’t a one-off act; it’s a lifestyle,” Tyson wrote. “Every day, ask yourself, ‘Am I becoming more like Christ, or just more efficient at what doesn’t truly matter?’ ‘Am I walking the path of life or the path of future regret?’”
3. Move forward and trust God for the results
“Trust in the Lord and do good; dwell in the land and enjoy safe pasture.” (Psalm 37:3)
When you spend a lot of time in the Land of Woulda, Coulda, Shoulda, as I have, you eventually reach for the advice that helps you break free. For me, it typically starts with this: Trust God and do the next right thing.
It’s a three-part challenge.
One, to trust God. Not just to say we trust God or to trust God in theory, but to fully surrender our will to His will with the confidence that He, because He is God and we’re not, has things under control no matter how messed up we find our lives.
Two, to take action. God calls us to be still and listen, but he also calls us to “do” what He would have us do. Deuteronomy 6:4 – “Hear, O Israel: The Lord is Our God, the Lord is One” – is the beginning of a traditional Hebrew prayer known as the “Shema,” a word that translates as “hear” or “listen.” But the Hebrew understanding of that word is much deeper. It means to let the words we are about to hear sink in, to understand them, and to act on them. Hearing and doing are simultaneous actions.
Three, to do the right thing. Remember when Jesus is praying and his disciples keep falling asleep? Jesus rebukes them, and eventually Judas shows up to betray Jesus and the time for praying is over. “Rise,” Jesus tells the disciples when Judas arrives, “let us be going.” (Matthew 26:46, NKJV)
The message to the disciples was to get up and move forward with Jesus.
“Arise and do the next thing,” as Oswald Chambers put it in My Utmost for His Highest. But not just any next thing. The next right thing. To quote Chambers again, “Never let the sense of failure corrupt your new action.”
The disciples didn’t exactly trust God and do the next right thing that night. Peter sliced a guy’s ear off and went on to deny he even knew Jesus, and everyone else ran for the hills. Jesus, meanwhile, went to the cross and then the grave. But Jesus didn’t stay in the grave, and, therefore, the disciples didn’t have to stay in the Land of Woulda, Coulda, Shoulda.